Reaction #90067

Reaction equation

(3-Cyano-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl)-propynoic acid methyl ester

Hydrochloric acid

→

title compound

Yield 66.0%

(3-Cyano-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl)-propynoic acid

Yield 66.0%

Solvents

methanol

THF

Conditions

Workup

1. 1
   Extractionwas then extracted with ethyl acetate
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried over magnesium sulfate
4. 4
   OtherThe solids obtained
5. 5
   Filtrationafter filtration and concentration under reduced pressure
6. 6
   Washwere washed with dichloromethane
7. 7
   Otherpurified by HPLC

Procedure

(3-Cyano-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl)-propynoic acid methyl ester (Compound E6-1, 15.2 mg, 0.038 mmol) was dissolved in a mixture solvent of methanol (1.5 mL) and THF (0.5 mL), added with 2 N aqueous solution of potassium hydroxide (5 drops), and then stirred at room temperature overnight. 0.5 N Hydrochloric acid was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solids obtained after filtration and concentration under reduced pressure were washed with dichloromethane and purified by HPLC to obtain the title compound (white solid, 9.6 mg, 66%).

Source